Submitted by Cynthia Ewer on August 27, 2016 - 10:53am Choices "Start"? What's that? I plan for the holiday season year-round. Summer is a great time to start holiday planning ... with plenty of time to prepare Back-to-school signals that the holidays aren't far behind. That's when I get ready. Halloween is a good time to get started without spoiling the excitement. I'm a purist: I wait until Thanksgiving is over before planning for Christmas. Mid-December. I know. I'm a procrastinator. Christmas Eve! I like the feeling of pressure.